CH522712A - Azo pyrazolone disperse dyes for polyester fibres - Google Patents
Azo pyrazolone disperse dyes for polyester fibresInfo
- Publication number
- CH522712A CH522712A CH1600968A CH1600968A CH522712A CH 522712 A CH522712 A CH 522712A CH 1600968 A CH1600968 A CH 1600968A CH 1600968 A CH1600968 A CH 1600968A CH 522712 A CH522712 A CH 522712A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- disperse dyes
- pyrazolone
- polyester fibres
- phenyl
- Prior art date
Links
- 239000000986 disperse dye Substances 0.000 title claims description 4
- 229920000728 polyester Polymers 0.000 title abstract description 9
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title description 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- MKMDCEXRIPLNGJ-UHFFFAOYSA-N 2-phenyl-1h-pyrazol-5-one Chemical compound N1=C(O)C=CN1C1=CC=CC=C1 MKMDCEXRIPLNGJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 7
- 230000008878 coupling Effects 0.000 abstract description 2
- 238000010168 coupling process Methods 0.000 abstract description 2
- 238000005859 coupling reaction Methods 0.000 abstract description 2
- 239000004744 fabric Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 1
- IMZSHPUSPMOODC-UHFFFAOYSA-N 5-oxo-1-phenyl-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=CC=C1 IMZSHPUSPMOODC-UHFFFAOYSA-N 0.000 abstract 1
- 229960004050 aminobenzoic acid Drugs 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 abstract 1
- 238000011282 treatment Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 238000009998 heat setting Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- FDPVTENMNDHFNK-UHFFFAOYSA-N 2-amino-n-phenylbenzamide Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1 FDPVTENMNDHFNK-UHFFFAOYSA-N 0.000 description 1
- QHWDUJPWCGEBTH-UHFFFAOYSA-N 4-amino-n-phenylbenzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1 QHWDUJPWCGEBTH-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XYQRXRFVKUPBQN-UHFFFAOYSA-L Sodium carbonate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]C([O-])=O XYQRXRFVKUPBQN-UHFFFAOYSA-L 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 229940018038 sodium carbonate decahydrate Drugs 0.000 description 1
- KEAYESYHFKHZAL-IGMARMGPSA-N sodium-23 atom Chemical group [23Na] KEAYESYHFKHZAL-IGMARMGPSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Preparation of compds. R = Me or Et; X is phenyl unsubstd. or substd. by halogen, alkyl or alkoxy. By diazotisation of the anilide of aminobenzoic acid and coupling into 1-phenyl-5-pyrazolone-3-carboxylic acid ester. Gives dyeings on polyester fabrics of deep shades having good fastness to heat-fixing treatments.
Description
Verfahren zur Herstellung von Dispersionsfarbstoffen
Aus vielen Veröffentlichungen, beispielsweise den Schweizer Patentschriften No. 386 590 und 389 803 und der französischen Patentschrift 1 157 660 ist bekannt, dass Azofarbstoffe !mit Pyrazolonderivaten als Kupplungskomponenten in vielen Fällen als Dispersionsfarbstoffe verwendbar sind. Es ist jedoch sehr schwierig, aus der Fülle der bekannten und denkbaren Farbstoffe dieses Prinzips solche Individuen herauszufinden, die auf Polyestermaterialien Färbungen mit einem den heutigen Ansprüchen genügenden Echtheitsniveau ergeben.
Sehr oft findet rman nämlich, dass sich gewisse Eigenschaften gegenläufig verändern; insbesondere trifft dies für das Ziehvermögen und die Thermofixierechtheit zu, denn weitgehend gilt die Regel, dass thermofixierechte Polyesterfarbstoffe der Azo-Pyrazolonreihe wenig ausgiebig sind gut ziehende Farbstoffe dagegen ungenügende Thermofixierechtheit haben.
Es wurd nun gefunden, dass man neue, insbesondere zum Färben von Polyestermaterial geeignete, gleichermassen ausgiebige und thermofixierechte Dispersions.
farbstoffe der Formel
EMI1.1
erhält, in der Ar einen gegebenenfalls durch Halogen, Alkvl- oder Alkoxygruppen subsitutierten Benzolring und R einen niederen Alkylrest bedeuten und wobei die Arylarnidgruppe in meta- oder paratellung zur Azobrücke steht, wenn man Aminobenzoesäureanilide der Formel
EMI1.2
diazotiert und auf 1-Phenyl-pyrazolon-(5)-carbonsäu- reester-(3) kuppelt.
Im einzelnen seien als Substituenten für Ar beispielsweise Chlor- oder Bromatome sowie Methyl-, Aethyl-, Propyl-, Methoxy- und Aethoxygruppen genannt. Für R kommt insbesondere eine Methyl-, Aethyl- oder Propylgruppe in Betracht.
Die erfindungsgemäss erhaltenen Farbstoffe sind vorzugsweise nach dem sogenannten HT-Verfahren zum Färben von Polyestermaterial, wie Fasern, Flocken, Fäden, Geweben und Gewirken geeignet. Die Färbungen haben ausgezeichnete Echtheitseigenschaften, insbesondere Thermofixierechtheiten.
In vielen Fällen erreicht man ein gutes Ziehvermö- gen der erfindungsgemässen Farbstoffe auch nach der Carn.ermethode, wenn man anstelle von Einzelfarbstoffen ein Farbstoffgemisch zum Färben verwendet
Im folgenden beziehen sich Angaben über Teile und
Prozente auf das Gewicht.
Beispiel I
24,2 Teile 3-AminoWbenzoesäure-m-anisidid werden in 100 Teilen 20 0/obiger Salzsäure mit der Lösung von 7,1 Teilen Natriumnitrit in 20 Teilen Wasser diazotiert.
Die klare Diazoniumsalzlösung gibt man bei 0-5 "C zu der Lösung von 23,5 Teilen 1-Phenylpyrazolon-(5) carbonsäure-(3)-äthylester in einer Natronlauge aus 150 Teilen Wasser und 4 Teilen Natriumhydroxyd. Anschliessend versetzt man mit 100 Teilen Natriumcarbo nat-deka-hydrat. Man saugt das abgeschiedene Kupplungsprodukt ab, suspendiert es in Wasser und sänert unter Kühlung mit Salzsäure an. Danach wird Farbstoff abgesaugt, neutral gewasohen und getrocknet. Man einhält 41,8 Teile, das sind 86,2 O/o der Theorie, eines gelben Farbstoffs, der auf Polyesterfasern nach dem HT-Verfaihren leine tiefe Färbung mit sehr guter Lichtund Thermofixierechtheit ergibt.
Die in den folgenden Tabellen angeführten Farbstoffe (der Beispiele 2-7 werden analog Beispiel 1 hergestellt.
EMI2.1
Farbton auf Beispe Nr. R1 Polyesterfasern
2 p-CH3 gelb
3 m-CH3 gelb
4 p-O0ll3 I1
5 m-OCH 1I
6 m-Cl "
EMI2.2
Parbton auf Beisp. Nr. R1 BolyesterfaSern
7 m-CH3 gelb
Beispiel 8
21,2 Teile 4-Auninobenzoesäure-anilid werden bei 10-15 C in 110 Teilen konzentrierter Schwefelsäure gelöst und bei +5 C allmählich mit einer aus 7,1 Teilen Natriumnitrit und 23 Teilen konzentrierter Schwefelsäure hergestellten Nitrosylschwefelsäure versetzt.
Man rührt eine Stunde bei +5 OC, verdünnt die Lösung mit einem Gemisch aus 20,4 Teilen Eisessig und 18,4 Teilen konzentrierter Schwefelsäure und gibt nach einer weiteren 1/2 Stunde alles auf 500 Teile Eis. Man erhält eine klare Diazolösung, die bei 0-5 C mit der Lösung von 23,5 Teilen 1-Phenyl-pyrazolon-(5)-carbonsäure-(3)- äthylester ind 135 Teilen Eisessig versetzt wird. Unter Zusatz von Eis stumpft man das Mineralsäure enthalten- de Gemisch mit 400/oiger Natronlauge ab, bis keine Diazoverbindung mehr nachzuweisen ist. Der abgeschiedene Farbstoff wird abgesaugt, neutral gewaschen und getrocknet. Man erhält 32,5 Teile, das sind 71,5 0/0 d.Th.
Der Farbstoff liefert auf Polyester eine farbstarke Gelbfärbung mit sshr guter Licht-, Thermofixier- und Waschechtheit
Process for the preparation of disperse dyes
From many publications, for example Swiss patent specifications no. 386 590 and 389 803 and French patent specification 1,157,660 it is known that azo dyes with pyrazolone derivatives as coupling components can be used as disperse dyes in many cases. However, from the abundance of known and conceivable dyes of this principle, it is very difficult to find those individuals who produce dyeings on polyester materials with a level of fastness that meets today's requirements.
It is very often found that certain properties change in opposite directions; This applies in particular to the drawability and the heat-setting fastness, because the rule largely applies that heat-setting polyester dyes of the azo-pyrazolone series are not very extensive, whereas dyes with good drawing properties have insufficient heat-setting fastness.
It has now been found that new, in particular suitable for dyeing polyester material, equally extensive and heat-setting-fast dispersions.
dyes of the formula
EMI1.1
obtained in which Ar is a benzene ring optionally substituted by halogen, alkyl or alkoxy groups and R is a lower alkyl radical and the aryl amide group is meta or parallel to the azo bridge when aminobenzoic acid anilides of the formula
EMI1.2
diazotized and coupled to 1-phenyl-pyrazolone- (5) -carboxylic acid ester- (3).
Examples of substituents for Ar are chlorine or bromine atoms and methyl, ethyl, propyl, methoxy and ethoxy groups. A methyl, ethyl or propyl group is particularly suitable for R.
The dyes obtained according to the invention are preferably suitable for dyeing polyester material such as fibers, flakes, threads, woven and knitted fabrics by the so-called HT process. The dyeings have excellent fastness properties, especially heat-setting fastness properties.
In many cases, the dyestuffs according to the invention have good drawability, even by the Carnic method, if a dyestuff mixture is used for dyeing instead of individual dyestuffs
The following refer to information about parts and
Percentages on weight.
Example I.
24.2 parts of 3-AminoWbenzoic acid-m-anisidide are diazotized in 100 parts of 20% of the above hydrochloric acid with a solution of 7.1 parts of sodium nitrite in 20 parts of water.
The clear diazonium salt solution is added at 0-5 ° C. to the solution of 23.5 parts of 1-phenylpyrazolone (5) carboxylic acid (3) ethyl ester in a sodium hydroxide solution composed of 150 parts of water and 4 parts of sodium hydroxide Parts of sodium carbonate decahydrate are filtered off with suction, suspended in water and acidified with hydrochloric acid while cooling. The dye is then filtered off with suction, washed neutral and dried. 41.8 parts, or 86.2%, are maintained / o the theory, of a yellow dye which, after the HT process, gives a deep dyeing on polyester fibers with very good fastness to light and heat-setting.
The dyes listed in the following tables (of Examples 2-7 are prepared analogously to Example 1.
EMI2.1
Color on Beispe No. R1 polyester fibers
2 p-CH3 yellow
3 m-CH3 yellow
4 p-O0ll3 I1
5 m-OCH 1I
6 m-Cl "
EMI2.2
Parbton on example no. R1 Bolyester fibers
7 m-CH3 yellow
Example 8
21.2 parts of 4-aminobenzoic acid anilide are dissolved in 110 parts of concentrated sulfuric acid at 10-15 ° C. and a nitrosylsulfuric acid prepared from 7.1 parts of sodium nitrite and 23 parts of concentrated sulfuric acid is gradually added at +5 ° C.
The mixture is stirred for one hour at +5 ° C., the solution is diluted with a mixture of 20.4 parts of glacial acetic acid and 18.4 parts of concentrated sulfuric acid and, after a further 1/2 hour, everything is added to 500 parts of ice. A clear diazo solution is obtained, to which a solution of 23.5 parts of 1-phenylpyrazolone (5) carboxylic acid (3) ethyl ester in 135 parts of glacial acetic acid is added at 0-5 ° C. With the addition of ice, the mixture containing mineral acid is blunted with 400% sodium hydroxide solution until no more diazo compounds can be detected. The deposited dye is filtered off with suction, washed neutral and dried. 32.5 parts are obtained, that is 71.5% of the theory.
On polyester, the dye gives a strong yellow coloration with very good fastness to light, heat-setting and washing
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0087564 | 1966-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH522712A true CH522712A (en) | 1972-05-15 |
Family
ID=6983852
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1600968A CH522712A (en) | 1966-06-15 | 1967-06-07 | Azo pyrazolone disperse dyes for polyester fibres |
| CH804467A CH478291A (en) | 1966-06-15 | 1967-06-07 | Dyeing of polyester textile material with disperse dyes of the pyrazolone series |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH804467A CH478291A (en) | 1966-06-15 | 1967-06-07 | Dyeing of polyester textile material with disperse dyes of the pyrazolone series |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3511828A (en) |
| CH (2) | CH522712A (en) |
| DE (1) | DE1544400A1 (en) |
| FR (1) | FR1527455A (en) |
| GB (1) | GB1185219A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107353669B (en) * | 2017-06-30 | 2018-11-06 | 深圳市国华光电科技有限公司 | A kind of weld, ink and electric moistening display |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3246945A (en) * | 1963-10-10 | 1966-04-19 | Gen Aniline & Film Corp | Method for dyeing polyesters |
-
1966
- 1966-06-15 DE DE19661544400 patent/DE1544400A1/en active Pending
-
1967
- 1967-06-06 US US643820A patent/US3511828A/en not_active Expired - Lifetime
- 1967-06-07 CH CH1600968A patent/CH522712A/en not_active IP Right Cessation
- 1967-06-07 CH CH804467A patent/CH478291A/en not_active IP Right Cessation
- 1967-06-14 GB GB27417/67A patent/GB1185219A/en not_active Expired
- 1967-06-15 FR FR110491A patent/FR1527455A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3511828A (en) | 1970-05-12 |
| FR1527455A (en) | 1968-05-31 |
| GB1185219A (en) | 1970-03-25 |
| CH804467A4 (en) | 1969-05-30 |
| CH478291A (en) | 1969-10-31 |
| DE1544400A1 (en) | 1969-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |